ethyl 1-[2-(benzyloxy)ethyl]-4-phenylpiperidine-4-carboxylate hydrobromide

• ChemBase ID: 161219
• Molecular Formular: C23H30BrNO3
• Molecular Mass: 448.3932
• Monoisotopic Mass: 447.14090583
• SMILES: C1C(CCN(C1)CCOCc1ccccc1)(C(=O)OCC)c1ccccc1.Br
• Canonical SMILES: CCOC(=O)C1(CCN(CC1)CCOCc1ccccc1)c1ccccc1.Br
• InChI: InChI=1S/C23H29NO3.BrH/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20;/h3-12H,2,13-19H2,1H3;1H
• InChIKey: CPEIQAXBGPGICQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-[2-(benzyloxy)ethyl]-4-phenylpiperidine-4-carboxylate hydrobromide
• IUPAC Traditional name: benzethidine hydrobromide
• Synonyms: 4-Phenyl-1-[2-(phenylmethoxy)ethyl]-4-piperidinecarboxylic Acid Ethyl Ester Hydrobromide; 1-[2-(Benzyloxy)ethyl]-4-phenylisonipecotic Acid Ethyl Ester HYdrobromide; 1-(2-Benzyloxyethyl)-4-phenylpiperidine-4-carboxylic Acid Ethyl Ester Hydrobromide; Benzethidin Hydrobromide; NIH 7574 Hydrobromide; Benzethidine Hydrobromide

Database IDs

• CAS Number: 1049728-53-1
• PubChem SID: 162255354
• PubChem CID: 5744992

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.5753652
• LogD (pH = 7.4): 3.3472648
• Log P: 4.133298
• Molar Refractivity: 108.1398 cm^3
• Polarizability: 42.440403 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B190100

A related compound of the opioid analgesic drug Meperidine (M223900) with similar effects such as analgesia, sedation, nausea and respiratory depression.

REFERENCES

• Cahal, D.A. et al.: Int. J. Obstet. Gynaecol., 68, 88 (1961)
• Maul, C. et al.: Analgesics, 159 (1961)